Alloc-All-OMe | 106928-48-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Alloc-All-OMe
• 英文别名: Methyl 2-<(allyloxycarbonyl)amino>-4-pentenoate；N-(allyloxycarbonyl)-DL-allylglycine methyl ester；Methyl N-(2-propenyloxycarbonyl)-2-amino-4-pentenoate；methyl 2-(prop-2-enoxycarbonylamino)pent-4-enoate
• CAS: 106928-48-7
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: AYRFSUNHTJSIBH-UHFFFAOYSA-N

物化性质

• 沸点：
  294.1±40.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Alloc-All-OMe 在 palladium diacetate 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 Methyl 2-<(allyloxycarbonyl)amino>-2-methoxyacetate
  参考文献：
  名称：

  Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

  摘要：

  DOI：

  10.1021/jo00290a015
• 作为产物：
  描述：

  甲基-2-Boc-氨基-4-戊烯酸 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 Alloc-All-OMe
  参考文献：
  名称：

  Selective transformation of N--butoxycarbonyl group into n-alkoxy-carbonyl group n-carboxylate ion equivalent

  摘要：

  DOI：

  10.1016/s0040-4039(01)80883-2

文献信息

• Tertiary-butyldimethylsilyl carbamate derivative and process for
  申请人：Suntory Limited

  公开号：US04837349A1

  公开（公告）日：1989-06-06

  A t-butyldimethylsilyl carbamate derivative and a process for producing the same are disclosed. Tertiary-butyldimethylsilyl carbamate derivatives having the following general formula (1) are intermediates for the production of a variety of carbamate esters that can be extensively used as drugs acting on the central nervous system or circulatory organs, as agrichemicals (e.g. insecticides and herbicides), or as antimicrobial agents; a process capable of economical and efficient production of such intermediates is also disclosed: ##STR1## where R.sup.1 is an alkyl group having 1-3 carbon atoms or a hydrogen atom; R.sup.2 is ##STR2## (where R.sup.3 is a hydrogen atom, an alkyl, alkenyl or aralkyl group having 1-10 carbon atoms, each of which groups may be substituted by a hydroxyl group, a t-butyldimethylsilyloxy group, a methylthio group, a lower alkoxycarbonyl group, a lower alkoxy group, an indolyl group or an imidazolyl group; R.sup.4 is a lower alkoxycarbonyl group, an N-alkylamido group having 2-6 carbon atoms, an O-tetrahydropyranylthr eonine methyl ester amido residue, an O-t-butyldimethylsilylthreonine methyl ester amido residue, a threonine methyl ester amido residue or --(CH.sub.2).sub.n --COOR.sup.5 (where n is an integer of 1-3 and R.sup.5 is a lower alkyl group), provided that R.sup.3 combines with R.sup.4 to form a cyclopentyl group, a cyclohexyl group, a tetrahydrofuranyl group or a dioxanyl group, these rings being optionally substituted by a lower alkyl group, a lower alkenyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonylmethyl group); and R.sup.1 and R.sup.2, when taken together, form a 4- or 5-membered carbon ring, which may be substituted by a lower alkoxycarbonyl group or a t-butyldimethylsilyloxycarbonyl group.

  本发明公开了一种t-叔丁基二甲基硅烷基氨基甲酸酯衍生物及其制备方法。具有以下通用式（1）的三叔丁基二甲基硅烷基氨基甲酸酯衍生物是制备多种可广泛用作中枢神经系统或循环器官药物、农药（例如杀虫剂和除草剂）或抗微生物剂的氨甲酯的中间体；本发明还公开了一种能够经济高效地生产这种中间体的方法： 其中，R1是具有1-3个碳原子的烷基或氢原子；R2是##STR2##（其中R3是氢原子、具有1-10个碳原子的烷基、烯基或芳基烷基，这些基团中的每一个都可以被羟基、t-叔丁基二甲基硅氧基、甲硫基、低级烷氧羰基基团、低级烷氧基、吲哚基或咪唑基取代；R4是低级烷氧羰基基团、具有2-6个碳原子的N-烷基酰胺基团、O-四氢吡喃基缩酰亮氨酸甲酯酰基、O-t-叔丁基二甲基硅基缩酰亮氨酸甲酯酰基、亮氨酸甲酯酰基或--（CH2）n--COOR5（其中n是1-3的整数，R5是低级烷基基团），前提是R3与R4结合形成环戊基、环己基、四氢呋喃基或二氧杂环己基，这些环可选地被低级烷基、低级烯基、低级烷氧羰基基团或低级烷氧羰基甲基基团取代；当R1和R2一起取时，形成一个4-或5-成员碳环，该环可以被低级烷氧羰基基团或t-叔丁基二甲基硅氧羰基基团取代。
• Tertiary-butyldimethylsilyl carbamate derivative and process for producing the same
  申请人：SUNTORY LIMITED

  公开号：EP0217243A2

  公开（公告）日：1987-04-08

  At-butyldimethylsilyl carbamate derivative and a process for producing the same are disclosed. Tertiarybutyl- dimethylsilyl carbamate derivatives having the following general formula (1) are intermediates for the production of a variety of carbamate esters that can be extensively used as drugs acting on the central nervous system or circulatory organs, as agrichemicals (e.g. insecticides and herbicides), or as antimicrobial agents; a process capable of economical and efficient production of such intermediates is also disclosed: where R1 is an alkyl group having 1 - 3 carbon atoms or a hydrogen atom; R2 is (where R3 is a hydrogen atom, an alkyl, alkenyl or aralkyl group having 1 - 10 carbon atoms, each of which groups may be substituted by a hydroxyl group, a t-butyldimethylsilyloxy group, a methylthio group, a lower alkoxycarbonyl group, a lower alkoxy group, an indolyl group or an imidazolyl group; R4 is a lower alkoxycarbonyl group, an N-alkylamido group having 2 - 6 carbon atoms, an O-tetrahydropyranylthreonine methyl ester amido residue, an O-t-butyldimethyl- silylthreonine methyl ester amido residue, a threonine methyl ester amido residue or -(CH2)n-COOR5 (where n is an integer of 1 - 3 and R5 is a lower alkyl group), provided that R3 combines with R4 to form a cyclopentyl group, a cyclohexyl group, a tetrahydrofuranyl group or a dioxanyl group, these rings being optionally substituted by a lower alkyl group, a lower alkenyl group, a lower alkoxycarbonyl group or a lower alkoxycarbonylmethyl group); and R' and R2, when taken together, form a 4- or 5-membered carbon ring, which may be substituted by a lower alkoxycarbonyl group or a t-butyldimethylsilyloxycarbonyl group.

  本发明公开了叔丁基二甲基硅基氨基甲酸酯衍生物及其生产工艺。具有以下通式(1)的叔丁基二甲基硅基氨基甲酸酯衍生物是生产各种氨基甲酸酯的中间体，这些氨基甲酸酯可广泛用作作用于中枢神经系统或循环器官的药物、农用化学品（如杀虫剂和除草剂）或抗菌剂；还公开了一种能够经济、高效地生产这种中间体的工艺： 其中 R1 是具有 1 - 3 个碳原子的烷基或氢原子；R2 是 (其中 R3 是氢原子、具有 1-10 个碳原子的烷基、烯基或芳基，每个基团可被羟基、叔丁基二甲基硅氧基、甲硫基、低级烷氧基羰基、低级烷氧基、吲哚基或咪唑基取代；R4 是低级烷氧基羰基、具有 2-6 个碳原子的 N-烷基氨基、O-四氢吡喃苏氨酸甲酯氨基残基、O-叔丁基二甲基硅基苏氨酸甲酯氨基残基、苏氨酸甲酯氨基残基或-(CH2)n-COOR5（其中 n 为 1-3 的整数，R5 为低级烷基）、条件是 R3 与 R4 结合形成环戊基、环己基、四氢呋喃基或二噁烷基，这些环可选择被低级烷基、低级烯基、低级烷氧羰基或低级烷氧羰基甲基取代）；R'和 R2 合在一起形成一个 4 或 5 元碳环，可被一个低级烷氧羰基或一个 t-丁基二甲基硅氧基羰基取代。
• Palladium-Catalyzed Transprotection of Allyloxycarbonyl-Protected Amines: Efficient One-Pot Formation of Amides and Dipeptides
  作者：Eric C. Roos、Pablo Bernabe、Henk Hiemstra、W. Nico Speckamp、Bernard Kaptein、Wilhelmus H. J. Boesten

  DOI：10.1021/jo00111a035

  日期：1995.3

  The synthetic utility of the N-(allyloxycarbonyl) (Alloc) substituent in alpha-amino acid derivatives is substantially extended beyond its well-known function as an amine protecting group. When the palladium-catalyzed deprotection is carried out by using tributyltin hydride as nucleophile (the Guibe method) in the presence of an active acylating agent a new acyl group is introduced on nitrogen. Successful acylating agents include carboxylic acid anhydrides, acid chlorides, and activated esters. A useful example of this methodology is the removal of the Alloc group in the presence of tert-butyl dicarbonate, which in essence amounts to a ''transprotection'' to a Boc-protected alpha-amino acid derivative. More importantly, the use of activated N-protected alpha-amino ester derivatives (e.g., pentafluorophenyl esters) leads to dipeptides. This new method for peptide coupling proceeds very fast under mild conditions, in good to excellent yields, and without noticeable racemization.
• Palladium-catalyzed synthesis of amides and peptides
  作者：Eric C. Roos、Pablo Bernabé、Henk Hiemstra、W.Nico Speckamp、Bernard Kaptein、Wilhelmus H.J. Boesten

  DOI：10.1016/0040-4039(91)80241-w

  日期：1991.11

  When the Pd(0)-catalyzed hydrostannolysis of the N-allyloxycarbonyl group is carried out in the presence of an activated carbonyl compound, a coupling product is formed. This new method appears to be applicable to the synthesis of a wide range of amides and peptides.
• US4837349A
  申请人：——

  公开号：US4837349A

  公开（公告）日：1989-06-06